- What are your plans for the next week?
- What you dream of doing but never get around to?
- What have you done lately that you can brag about??
- And you told someone you were going on a date?
- What would you advise yourself to do right now as a school-age student?
- What do you like about dating and what don’t you like?
- What day of your life would you like to repeat?
- What you are known for among your friends?
- The stereotype about young men or girls that pisses you off the most
- If you had the option of not working, how would you spend your days?
- What can make you nervous??
- What can immediately frustrate you about the person??
- The most ridiculous thing you’ve ever googled
- You have scars that have interesting stories associated with them?
- The best advice you’ve ever given in your life
- Is it possible friendship between a man and a woman??
- What do people most often get wrong when describing you??
- A job you could never do
- Your favorite place to go on weekdays, where you’re willing to go anytime you have a free minute
- How you met your best friend?
- The most vivid childhood memory
Many people ask questions on a first date just to keep the conversation going, but if you pick them right, you can learn a lot of interesting things about your date. Maybe even decide if this person is right for you or not.
Here’s a list of questions that will help you do this best.

What are your plans for the next week?
This is a delicate way to see if he plans to meet with you again soon. With it, you can look into his interests, find out what his ordinary life consists of, what things matter to him.
What you dream of doing but never get around to?
This is a trick question, which can reveal your partner from an unexpected side. He may say that he has always dreamt of scuba diving or being in a real desert. And it may turn out that the man has no aspirations and desires, or he begins to share intimate fantasies.
In any case, finding out about the dreams of a companion, you can compare them with your own and determine whether they coincide in you.
What have you done lately that you can brag about??
This question helps to determine a person’s life values, to understand what is important to him, and what is secondary. Besides, if the answer turns into a whole eulogy about yourself, it can be interpreted as narcissism. This is a quality that will definitely show up in a relationship, which is worth considering from the start.
And you told someone you were going on a date?
Another trick question, the answer to which may surprise you. Perhaps your date right now is being broadcast live and is being discussed by all his followers. Or he wrote about meeting his ex-girlfriend to piss her off.
Or maybe he is a private person and no one knows about your acquaintance and meeting yet. Either way, this question will also help you learn something new about your companion.
What would you advise yourself to do right now as a school-age student?
If a young man has a lot of experience with the opposite sex, he can advise himself to date several girls at the same time. Or on the contrary, will tell you not to be distracted from your studies because of the relationship.
Depending on what exactly your date will say, you can understand his attitude towards the opposite sex, which will affect your communication.
What do you like about dating and what don’t you like?
This question may seem too general. But it helps to understand the degree of openness and sociability of a man. For example, if he says he likes to date and visit fancy places in the city, you certainly won’t be bored with him in the future, provided that you also like to spend time away from home.
And it is possible that you will hear that the young man does not like to date, because it is necessary to waste precious time on a stranger, or that there is nothing better than an evening at home.
In any case, you will be able to assess the level of sociability of your companion and make predictions about how your meetings will go in the future.
What day of your life would you like to repeat?
Will allow you to assess your companion’s priorities and values, and learn more about his interests. It all depends on what he would like to repeat, an extreme kayaking or a last night reunion of classmates.
Or maybe you’ll hear that he thinks every day is beautiful and doesn’t look back, which characterizes him as someone who isn’t prone to sentimentality.
What you are known for among your friends?
You could be the hero of jokes about being able to drink a liter of beer in half a minute or loving going on dates with new girls every day. And maybe the young man has a reputation as a friend who always comes to the rescue and will not abandon in a difficult time.
Here you should also pay attention to how willingly the man talks about himself and his merits. If he does it too inspirationally, that’s another hidden signal of excessive self-love.
The stereotype about young men or girls that pisses you off the most
Such a question will help you understand how a person generally feels about the opposite sex, as well as determine the approximate scenarios he usually employs in a relationship. Such observations can be compared with your views and check how well suited you are for this person.
For example, if he tells you that a man doesn’t have to provide for the family, it has to be both of them, you can count on a quiet partnership. But if he tells you that a woman’s duty is to stay home and provide comfort, you may have to fight for your rights if your communication leads to marriage.
Either way, you can make certain predictions based on his answer to this question and make a decision about further communication.
If you had the option of not working, how would you spend your days?
This question helps to determine the person’s values and ambitions. After all, not everyone can boast that work is his hobby. So, freed from the obligation of earning, perhaps a man would take up self-development or be out fishing all the time. The main thing is that he should have some interests and aspirations.
And if he tells you that he would sleep or watch TV all day, you should be careful, because it is obvious that the person lacks motivation and serious goals. But on the other hand, if this is also your perfect day, you may have found each other.
What can make you nervous??

It helps to find your partner’s vulnerabilities and get to know him better in general. He might be afraid of heights, or of public speaking, spiders, or clowns. It also matters what form of response he constructs. If it’s a serious story about being frightened as a child by a clown in a circus, the person really has a psychological trauma that needs to be worked out. And if he talks about his fears with humor and recalls funny moments associated with them, it shows that he knows how to hold his own, even in difficult moments.
What can immediately frustrate you about the person??
A question that can be used to determine the degree to which he is loyal to the shortcomings of others and the ability to respond calmly to them. For example, if he tells you that he hates it when people lie, and he can’t communicate with a girl who has lied to him, this is an adequate answer.
And if he does not accept that the chosen one has a relationship in the past, it is already a reason to think, why he is so intolerant, and will it be possible to build with him a strong relationship?.
The most ridiculous thing you’ve ever googled
A question to test a sense of humor, which, on the other hand, will help you get to know the person better. The dialogue can turn into a funny story about what interesting things were found on the Internet. But here you also have to be prepared for the fact that the answer might be too unexpected and perhaps even unpleasant.
And it’s good if such moments are revealed at the initial stage of communication – so you will not have unnecessary illusions, and you can make an informed decision about the readiness for further communication.
You have scars that have interesting stories associated with them?
This is a rather personal question that is hardly appropriate on a first date. But if you ask it correctly, you can learn a lot of useful things. For example, a young man will tell an interesting story from his childhood that can be discussed and the conversation will be effortlessly sustained.
But if he tells you about the scars from stab wounds received in street fights, that’s a reason to wonder why the man gets into trouble so often and why he’s proud of it.
The best advice you’ve ever given in your life
With this question you give the man a chance to brag, and you can check to see how he takes advantage of it. In addition, he will think he is talking about something important and wise, but in fact he is showing what problems are bothering him now or in the past.
Is it possible friendship between a man and a woman??
A trick question, which is likely to lead to a heated discussion about the relationship between the sexes. In addition, his response will show how well he knows how to maintain relationships after a breakup, as well as determine the risk of having ex-girlfriends in his life with whom he continues to communicate “as a friend”. This will allow you to determine if you’re ready for such a turnaround, or if it’s better to look for a guy who, after a breakup, does put a point on the communication.
What do people most often get wrong when describing you??
A question that can identify different red flags. For example, your companion will tell you that many people think he is too categorical and inflexible. Naturally, it is worth asking why people have this opinion. In response, you might hear an entertaining story that would be interesting to discuss. But it’s worth listening to the story carefully; you might hear something you can’t put up with in a relationship.
A job you could never do
Help determine the man’s values, his interests and stereotypes. For example, if he says there’s no way he could teach dance because it’s a woman’s occupation, it shows stereotypical thinking that can create communication difficulties. He may also say he couldn’t work for an animal trapping service, a clear demonstration of his kindness and love for our lesser brethren.
Your favorite place to go on weekdays, where you’re willing to go anytime you have a free minute
A question with which you can find common ground or, conversely, understand that in a relationship will be difficult. Everyone prefers to relax in different ways, for example, if the best thing for you to spend the evening together at home, and for him to go to the club, you are unlikely to be comfortable with each other.
How you met your best friend?
The well-known saying that you can judge a person by a friend does not lose its relevance. From the answer you can learn more about his character, his habits, his views on different things. All of which will help make predictions about the prospects of your communication.
It is also possible that he will answer that he does not believe in friendship, or that he has never found a true friend. The first speaks of distrust of the world, and the second, perhaps, of exaggerated demands on those around you.
The most vivid childhood memory
That way you can learn a little bit about his family, their traditions and the principles of parenting. For example, if his mother was constantly controlling him, maybe she is controlling his life now.
On the other hand, childhood is almost everyone’s favorite time. And this question will help your interlocutor be transported back to that time, and you can learn more about his or her views on life.
So, even on a first date you can learn quite a lot about a person if you build a dialogue correctly. Leading questions and casual conversation help you learn a lot about the person you are talking to, and allow you to assess the prospects for communicating with him or her.